AFCDB: Indole (FDB012008)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:56 UTC

Update date

2019-11-26 03:05:57 UTC

Primary ID

FDB012008

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Indole

Description

Constituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs Indole is a major constituent of coal-tar, and the 220-260 °C distillation fraction is the main industrial source of the material. Indole and its derivatives can also be synthesized by a variety of methods. The main industrial routes start from aniline.; Indole is a solid at room temperature. Indole can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. It also occurs in coal tar.; Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an indole ring are called indoles. The most famous derivative is the amino acid tryptophan.; Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. It can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine.; The Leimgruber-Batcho indole synthesis is an efficient method of sythesizing indole and substituted indoles. Originally disclosed in a patent in 1976, this method is high-yielding and can generate substituted indoles. This method is especially popular in the pharmaceutical industry, where many pharmaceutical drugs are made up of specifically substituted indoles.; The name indole is a portmanteau of the words indigo and oleum, since indole was first isolated by treatment of the indigo dye with oleum. Indole is found in many foods, some of which are flaxseed, agar, american pokeweed, and pear.

CAS Number

120-72-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.31 g/L	ALOGPS
logP	2.29	ALOGPS
logP	1.64	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	14.71	ChemAxon
pKa (Strongest Basic)	4.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	39.13 m³·mol⁻¹	ChemAxon
Polarizability	12.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H14N2

IUPAC name

1H-indole; 3H-indole

InChI Identifier

InChI=1S/2C8H7N/c2*1-2-4-8-7(3-1)5-6-9-8/h1-4,6H,5H2;1-6,9H

InChI Key

AYVVZVSBYJTFGL-UHFFFAOYSA-N

Isomeric SMILES

C1C=NC2=C1C=CC=C2.N1C=CC2=C1C=CC=C2

Average Molecular Weight

234.2958

Monoisotopic Molecular Weight

234.115698458

Classification

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Benzenoid
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Imine
Aromatic heteropolycyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 82.02%; H 6.02%; N 11.96%	DFC
Melting Point	Mp 52°	DFC
Boiling Point	Bp5 122.5-124°	DFC
Experimental Water Solubility	3.56 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.14	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 16.97 (25°,NH, KOH aq.)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	295 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16881

Phenol-Explorer ID

Not Available

DrugBank ID

DB04532

HMDB ID

HMDB00738

CRC / DFC (Dictionary of Food Compounds) ID

HCM26-E:HCM26-E

EAFUS ID

1794

Dr. Duke ID

INDOLE

BIGG ID

Not Available

KNApSAcK ID

C00001418

HET ID

IND

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
anti acne	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti streptococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
carcinogenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	DUKE
Insectiphile	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
tumorigenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
mothball	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
burnt	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
jasmine	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
honey	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fishy	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
animal	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
moth ball	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fecal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
naphthelene	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Indole (FDB012008)

Structure for FDB012008 (Indole)